Crossroads

Crossroads (2002) is Tamra Davis' coming-of-age road movie, and you can watch it online on iFILM. It's Britney Spears' big-screen debut: she plays Lucy, a straight-A graduate from small-town Georgia who, on prom night, digs up a childhood time capsule she once buried with two estranged friends.

That dare pulls Lucy back together with pregnant Kit and rebellious Mimi for a cross-country drive to Arizona — part chasing dreams, part settling old scores. Behind the wheel of the convertible is charming Ben (Anson Mount), whose finances nobody can quite explain. Expect a karaoke contest, blowups, a first romance and a few hard family truths along the way. Dan Aykroyd, Kim Cattrall, Zoe Saldana and Justin Long pop up in smaller parts.

Here's the surprise: the script came from Shonda Rhimes, years before Grey's Anatomy, which gives this road trip a stranger pedigree than it lets on. Critics weren't kind, but the film has aged into an early-2000s time capsule that still hits home for anyone who grew up on Spears' singles. Light, earnest, easy to love on a quiet night. Stream Crossroads (2002) online on iFILM.